Giancarlo Petrazzuolo defeated Pablo Santos 1-6 7-5 7-5 in the Egypt F2 qualifying round on clay. The upset overturned the form book — Pablo Santos came in leading the head-to-head 1–0, but Giancarlo Petrazzuolo had been the form player, winning 3 of their last 6 on clay. Giancarlo Petrazzuolo claimed a first win over Pablo Santos in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-07-07 | Italy F21 | SF | clay | Pablo Santos | 7-6(5) 6-3 |